1113-69-5

Basic information

• Product Name: 1,1-BIS(TRIFLUOROMETHYL)-2,2-DICYANOETHYLENE 97
• Synonyms: 1,1-BIS(TRIFLUOROMETHYL)-2,2-DICYANOETHYLENE 97;(2,2,2-trifluoro-1-(trifluoromethyl)ethylidene)-propanedinitril;(2,2,2-trifluoro-1-(trifluoromethyl)ethylidene)propanedinitrile;1,1-Bis(trifluoromethyl)-2,2-dicyanoethylene 97%;2-(1,1,1,3,3,3-hexafluoropropan-2-ylidene)propanedinitrile;2-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]malononitrile
• CAS NO: 1113-69-5
• Molecular Formula: C₆F₆N₂
• Molecular Weight: 214.0680192
• Mol File: 1113-69-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 107
• Flash Point: 90.6°C
• Appearance: /
• Density: 1.479
• Vapor Pressure: 0.0831mmHg at 25°C
• Refractive Index: 1.3528
• CAS DataBase Reference: 1,1-BIS(TRIFLUOROMETHYL)-2,2-DICYANOETHYLENE 97(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-BIS(TRIFLUOROMETHYL)-2,2-DICYANOETHYLENE 97(1113-69-5)
• EPA Substance Registry System: 1,1-BIS(TRIFLUOROMETHYL)-2,2-DICYANOETHYLENE 97(1113-69-5)

Safety Data

• Hazard Codes: Harmful:
• Hazardous Substances Data: 1113-69-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C6F6N2/c7-5(8,9)4(6(10,11)12)3(1-13)2-14

Upstream product

• 489412-29-5 7-(1-methylethylidene)-3,3-bis(trifluoromethyl)bicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile 
• 1585-86-0 (Hydroxy-bis-trifluormethyl-methyl)-malononitril 

Downstream Products

• 1158-50-5 1,1-Dicyano-2-phenyl-4,4-bis-(trifluormethyl)-cyclobutan 
• 1585-83-7 3,4-dimethyl-6,6-bis(trifluoromethyl)cyclohex-3-ene-1,1-dicarbonitrile 
• 131792-40-0 2-(1-Phenyl-allyl)-2-(2,2,2-trifluoro-1-trifluoromethyl-ethyl)-malononitrile 
• 134539-79-0 2-(Methylsulfanyl-phenyl-methyl)-2-(2,2,2-trifluoro-1-trifluoromethyl-ethyl)-malononitrile 
• 100036-08-6 2-Phenyl-6,6-bis-trifluoromethyl-cyclohex-3-ene-1,1-dicarbonitrile 
• 128309-67-1 N,N-Dimethyl-4-<2,2-dicyano-1,1-bis(trifluoromethyl)ethyl>aniline 
• 132607-52-4 C₂₃H₁₅F₆N₅O₂ 
• 124225-89-4 (η5-C5H5)(PPh3)2(C2PhC(CF3)2C(CN)2)Ru 
• 129646-59-9 (η5-C5H5)(PPh3)(C2PhC(CF3)2C(CN)2)Ru}2(C2(CN)2(CF3)2) 
• 129571-03-5 (η5-C5H5)(PPh3)(C2PhC(CF3)2C(CN)2)Ru}2(C2(CN)2(CF3)2) 
• 89952-16-9 [Pd(CNC₆H₃-2,6-Me₂)2((CN)2CC(CF₃)2)] 

Relevant articles and documents

Reaction of 2,2-bis(trifluoromethyl)-1,1-dicyanoethylene with 6,6-dimethylfulvene: Cycloadditions and a rearrangement

Reaction of 2,2-bis(trifluoromethyl)-1,1-dicyanoethylene (BTF;1) with 6,6-dimethylfulvene (2) affords the expected Diels-Alder cycloadduct, 7-(1-methylethylidene)-3,3-bis(trifluoromethyl)bicyclo[2.2.1]- hept-5-ene-2,2-dicarbonitrile (3), in good yield. The cycloadduct 3 is unstable and exists in equilibrium with the starting materials in less polar solvents. In more polar environment, the [4 + 2] adduct 3 either reverts to starting materials, or, in a competing process, is converted to the formal [2 + 2] adduct, 2-(1-methylethylidene)-7,7- bis(trifluoromethyl)bicyclo[3.2.0]hept-3-ene-6,6-dicarbonitrile (6). In the presence of acid, 3 is converted to a third isomeric form, 1,3a,5,6-tetrahydro- 7-methyl-5,5-bis(trifluoromethyl)-4H-indene-4,4-dicarbonitrile (8). Both 6 and 8 are formed with complete regiospecificity. Quantum mechanical calculations and X-ray crystallographic studies of this ensemble of reactions by BTF, and the analogous set of reactions by its progenitor, tetracyanoethylene (TCNE), reveal several interesting facets. The conversion of 3 to 6 occurs in certain polar solvents, in the presence of silica gel and alumina, as well as in the solid state. Single crystals of 3 were observed by X-ray crystallography to undergo crystal-to-crystal rearrangement to 6. The conversion of 3 to 8 proceeds by the initial retro-Diels -Alder reaction followed by isomerization of the fulvene to 1-isopropenyl-1,3-cyclopentadiene that then reacts with BTF to give the alternative Diels-Alder product as a single regioisomer. A hybrid density functional theory (DFT) method at the B3LYP/6-31G(d) level of theory gave calculated relative energies of 0.0, -9.0, and -18.8 kcal/mol for 3, 6, and 8, respectively. The same method was also used to correctly predict the regiochemical outcome of the cycloaddition of BTF with 1-isopropenyl-1,3-cyclopentadiene. Finally, an explanation is offered for the preference of the persubstituted cyanoolefins BTF and TCNE to add to the exocyclic diene portion of 1-isopropenyl-1,3-cyclopentadiene and the contrasting preference of 2-acetyloxy-2-propenenitrile to add to the endocyclic diene.